
Leverage “The Princess Bride” Strategies to Supercharge Your Business – NOW!
If you are trying to build your business, you might be surprised to find that The Princess Bride has some great lessons that can help you find success, inspiration, and, yes, more profits.
Here are TEN lessons you can apply starting today.
1 - It might take you a while to really succeed:
The Princess Bride was published in 1973. It was immediately optioned for a movie but one studio after another failed to get it made. Various directors including Richard Lester, Norman Jewison, John Boorman, Francois Truffaut – even Robert Redford were at some point rumored to direct. Production was on and off for over 10 years until Rob Reiner bought the production rights – with a financial assist from Norman Lear, who gave Reiner his start when Lear directed Reiner in “All in the Family.”
The film was released to theatres in September 1987. It was a modest success at the box office and a critical favorite. It was not until it was released on video a year later that it began its trip to cult classic. Thirty years after its video release, The Princess Bride still attracts new audiences.
How you can apply this: success might be right around the corner. Be willing to persevere and take time to find your groove (and audience) and build your business into the success it can be.
2 - You don’t need an all-star cast, but you do need talent:
The relatively low budget of the movie meant that director Rob Reiner had to recognize undervalued, unknown talent and create a cast of future all-stars. He leveraged a great script and combined it with great casting to create a film that was greater than the sum of its parts.
“The Princess Bride” featured a cast of mostly then-unknowns including Robin Wright, Carey Elwes, Chris Sarandon, Christopher Guest, and Wallace Shawn. Probably the best-known cast members (Fred Savage, Billy Crystal, Peter Falk, and Carol Kane) were in cameo roles. Fun fact, Cary Elwes was acting in a historical drama in Berlin when he auditioned for the role of Wesley. Reiner knew he had the Errol Flynn-good looks to pull off the role but was concerned that Elwes might not have the comedy chops. Elwes nailed the role when he pulled off a dead-on “Fat Albert” routine.
Robin Wright had a small role in a daytime soap opera at the time she was cast – and beat out nearly 500 other women who auditioned for the role including Whoopi Goldberg, Courtney Cox, and Meg Ryan.
Mandy Patinkin was known primarily to Broadway audiences – but director Rob Reiner was such a fan that he offered Patinkin any role he wanted. Patinkin chose Inigo Montoya because he had lost his father to cancer and the role reverberated with him. (Buzz Feed – 43 Inconceivable Facts about The Princess Bride)
How you can apply this: Leverage YOUR talent to solve the problems that your audience has. Your audience is hungry for a solution that only you can provide. Your talent is your superpower as you build your own business.
3 - Your biggest fans will be your best viral advertising and promotion:
“The Princess Bride” became a word-of-mouth success because of its fans. They love to quote the film and recite parts of the dialogue back and forth. Fans argue passionately about their favorite characters and scenes. Fans convert friends who have not seen the movie into new fans.
In a nod to Internet popularity, according to director Rob Reiner, Mandy Patinkin (Inigo Montoya) is still asked at least once a day to quote his most famous line: "Hello, my name is Inigo Montoya. You killed my father. Prepare to die."
In an interview with The New Yorker, Cary Elwes speculated that if social media had been around at the time the movie was released, it would have been a much bigger box-office hit.
How you can apply this: Create genuine connections with your audience. Ask them to help spread the word and build your business. When a friend refers another friend to your business, there is something called "the halo effect," which means that the friend automatically trusts your business because they trust the person who referred them.
4 - Fan popularity can gain you official credibility:
From its modest beginnings, it has endured, listed on the American Film Institute's “100 Laughs,” “100 Passions,” and nominated for “100 Movie Quotes” and “10 Top 10” lists.
Fans routinely vote for The Princess Bride for a variety of awards. More fans mean more opportunities to be nominated. The owners of The Princess Bride keep their fans engaged and their fans return the favor by keeping the movie popular.
Since its release on video in 1988, approximately eight “special edition” and behind-the-scenes versions with exclusive content have been released. Short features, cast interviews, varying cover art, and games keep interest high – and fans buying new copies.
There are websites, fan clubs, YouTube videos, Facebook pages, and countless Pins and memes with The Princess Bride themes. You can buy Princess Bride t-shirts, mugs, tote bags, and chocolates. Fan engagement continues to increase.
How you can apply this: Enough raving fans can drive your business to the top of Google or Amazon rankings. Raving fans who engage with your content can make it go viral. Build your business with trust, engage your audience with helpful content and advice, and your audience will respond.
5 - If you make it memorable, fans will want to take part. Great content (dialogue) rules:
- “As you wish.”
- “Inconceivable.”
- "Hello, my name is Inigo Montoya. You killed my father. Prepare to die."
- “Mawwiage, mawwiage is whha bwings us togewether today.”
- “You fell victim to one of the classic blunders - The most famous of which is "never get involved in a land war in Asia" - but only slightly less well-known is this: "Never go in against a Sicilian when death is on the line"!”
- “Death cannot stop true love. All it can do is delay it for a while.”
What gave The Princess Bride great quotability? Great content. The movie is well written with unexpected turns of phrase, sharp observations, and tag lines. All the elements of great content regardless of the media.
Ask any fan, they will probably each have their own favorite scene or quote. Mine is Wallace Shawn and Carey Elwes facing off in the poison cup scene.
Cary Elwes said an Iraq war veteran’s commanding officer used to send his troops off with a hearty “Have fun storming the castle” and a wave to inject a little humor into an otherwise deadly routine.
How you can apply this: Find unique ways to interact with your audience as you build your own business. Create content, training, videos and more that are so good that your audience can't help but remember it - and your business.


6 - Competitors can become allies when interests align:
Carey Elwes's character, The Dread Pirate Robert aka Westley, and Mandy Patinkin, Inigo Montoya, start out as enemies. In one of the epic scenes of the movie, they have a three-minute sword fight. Smartly, the book and movie treat them as equally skilled and gentlemanly. No low blows or anger. When Inigo is defeated, Westley doesn’t kill him (telling him it would be like smashing a beautiful stained glass window) but knocks him unconscious and continues his mission.
When Inigo regains consciousness, he and Fezzik (the giant) follow after Westley and rescue him from the Pit of Despair. They take the “mostly dead” Westley to the Miracle Max, the local wizard. Max has no initial incentive to help – in fact, he wants to remain uninvolved. Not until he realizes that helping Wesley and Inigo can defeat and humiliate the king is he willing to revive Wesley.
Westley wants to rescue Buttercup. Montoya wants to find the man who killed his father. Once they realize that the people who stand in their way are teamed up, Westley and Montoya set aside their differences and work toward their separate happily ever afters.
How you can apply this: Find complementary businesses that have an overlapping market. Dog trainers can team up with dog treat bakers. Custom cake creators can team up with wedding planners. Every business has another industry that has an overlap. Find that and team up so you can both build your business, make more sales, and get more exposure.
7 – If you are passionate about your quest, others will get on board:
Inigo Montoya has wanted one thing since he was a child: to avenge his father’s death. Westley has wanted one thing since he met Buttercup: to love her forever. Regardless of the obstacles, they both single-mindedly pursued their goals. They did not let Facebook updates or binge-watching Game of Thrones derail their quests.
Because of their passion, it is easier for others to follow and become part of the quest.
How you can apply this: Be authentic with your audience. Give behind-the-scenes access. Talk about how you have been baking cakes, training dogs, or sewing clothes since your grandmother/uncle/next door neighbor taught you when you were a kid. Show your passion and enthusiasm. It will shine through as you build your business.

8 – Don’t be afraid to ask for help:
Fezzik (Andre the Giant) had no real reason to help Westley and Inigo – but as unlikely as it seemed, the member of The Brute Squad was enchanted by the romantic quest.
Miracle Max (Billy Crystal) and Valerie (Carol Kane) had no incentive to revive Westley, but they also came to believe in the power of Westley’s love for Buttercup.
How you can apply this: If your business needs a boost, put out a call and ask every customer to refer you to one friend. If you are trying to raise money for a community cause that is close to your heart, ask your audience to be part of it. Turn your engagement into a conversation rather than a monologue.
9 – Hook them on the story and keep ‘em coming back for more:
What many people forget is that The Princess Bride is actually framed within a story told by a grandfather (Peter Falk in a small role) to a grandson (Fred Savage) home sick from school. The grandson is initially resistant to hearing the story since he does not think he wants to hear a love story. The grandfather starts reading the book – and soon the grandson is hooked.
When the grandfather offers to stop reading, the grandson begs him to continue. Great storytelling wins – and keeps ‘em coming.
Going back even further to the original manuscript, the book is framed as a retelling of an older folk tale – even though it is new material.
How you can apply this: Share your story. Talk about how you've been passionate about the environment since you did that middle school project and how that inspired you to make recycling a big part of your meal delivery service. Customers love it when they understand what drives you.
10 – Be willing to step outside your comfort zone. You might be surprised at what is waiting:
The grandson does not want to hear the story until he does. Buttercup does not believe that Westley is still alive and jumps off a cliff, surprised to find Westley following her rolling down the hill. Inigo Montoya does not want anyone to interfere with his mission to kill the six-fingered man until he realizes that he and Westley can become an even more powerful team.
As for the actors, neither Mandy Patinkin nor Cary Elwes had any experience of sword fighting. They devoted themselves so thoroughly to lessons that the only stunt doubles used were for the somersaults during the fight. It would have been easy (and probably cheaper for the production insurance) if they handed the sword fight to professionals. Both Elwes and Patinkin have said it was one of the most enjoyable parts of making the movie.
How you can apply this: If you see other businesses in your space doing TikTok or Facebook Live, try it for yourself. Even if doing video makes you uncomfortable. If other businesses are writing ebooks, try putting one together, even if you don't think you could be an author.
You may find that you are a natural on camera or that seeing your book published is pretty cool. You may also find a lucrative new niche or new audience to build your business.
11 – BONUS – You can want what you want, but you must be prepared.
Westley was a farm boy whose only skill was pleasing Buttercup when he left to seek his fortune. After being captured by pirates, Westley learned the skills that would allow him to reunite with Buttercup: sword fighting, immunity to iocane, hand-to-hand combat, and the ability to lead people. He became the hero who could defeat the evil enemies keeping them apart – and threatening Buttercup.
Farmboy Westley would have been killed; Dread Pirate Roberts was ready.
Inigo Montoya was the son of a swordmaker. He was 10 years old when the six-fingered man killed his father. At 10 years old, he was no match for the older man.
When Inigo finally finds and confronts the man who killed his father, he has been preparing all his life.
How you can apply this: Know what you want - and what you have to do to make it happen. Wishing won't make it so. It takes work and dedication. Goals are wishes with deadlines.
More ways to apply the lessons of The Princess Bride
The Princess Bride is a movie that came out nearly 30 years ago. How did a fairy tale about lost love, a masked pirate hero, a sword fighter avenging a murder, a giant, and rodents of unusual size not just survive – but thrive?
Why do fans not born when the movie first arrived in theatres regularly recite dialogue and attend special midnight theatre showings?
With some not-so-magic ingredients: great content, great delivery, and attention to the fan base.
First: great content.
Whether you are writing a technical manual or an advertisement, your first duty is to create something that not only serves the needs of your reader/viewer but also delivers an unforgettable experience.
Think a user manual can’t be great?
Switch things up and add stories, humor, and make it interactive. Your user manual doesn't have to be dry and dull. Make your user manual sparkle.
Southwest Airlines is famous for the way they present the mandatory safety demonstration. No stodgy video or (obviously) bored flight attendants. They add all sorts of fun elements to get people to pay attention and ENJOY the safety presentation. So yes, you can make almost anything entertaining.
Next, deliver a great experience.
Make every interaction with your business fun, pleasant, and memorable. Delivering a great experience does not have to be expensive or complicated.
It can be as simple as an unexpected extra "treat" in a sample box or a free cupcake when someone picks up their coffee order. It doesn't have to be big. Even little touches can help you grow your business - and gain new fans.
Pay attention to your (raving) fans.
The Princess Bride's fan base attention is unusual in that the fans continue promoting the movie. Sure, the studio helps things along with new releases. The actors don’t avoid their association with the movie. Carey Elwes just wrote a book about being on the set and toured for its release.
Mandy Patinkin says he gets stopped almost daily to recite his famous line - and he loves it!
You can harness the same type of fan loyalty in your business, too.
What do your fans treasure about your business? About your products? What can you get them excited about?
Your fans want to support you and your business. Help them by giving them something to be excited about and promote to their friends.
So next time you watch The Princess Bride, pay attention to all the ways you can apply their smart decisions in your business.